Structural analysis of enniatin H, I, and MK1688 and beauvericin by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and their production by Fusarium oxysporum KFCC 11363P

References

• Bottalico , A , Logrieco , A , Ritieni , A , Moretti , J , Randazzo , G and Corda , P . 1995 . Beauvericin and fumonisin B1 in preharvest Fusarium moniliforme maize ear rot in sardinia . Food Addit. Contam , 12 : 599 – 607 .
   PubMed Web of Science ®Google Scholar
• Careri , M , Mangia , A and Musci , M . 1996 . Applications of liquid chromatography-mass spectrometry interfacing systems in food analysis: pesticide, drug and toxic substance residues . J Chromatograph A , 727 : 153 – 184 .
   PubMed Web of Science ®Google Scholar
• Castella , G , Munkvold , GP , Imerman , P and Hyde , WG . 1999 . Effect of temperature, incubation period and substrate on production of fusaproliferin by Fusarium subglutinans ITEM 2404 . Natural Tox , 7 : 129 – 132 .
   PubMedGoogle Scholar
• Chelkowki , J and Lew , H . 1992 . Fusarium species of Liseola section-occurrence in cereals and ability to produce fumonisins . Microbiologie Aliments , 10 : 49 – 53 .
   Google Scholar
• Cooper , HJ , Hudgins , RR and Marshall , AG . 2004 . Electron capture dissociation Fourier transform ion cyclodepsipeptides, branched peptides, and ε-peptides . Int J Mass Spectrom , 234 : 23 – 35 .
   Web of Science ®Google Scholar
• Ganassi , S , Moretti , A , Bonvicini Pagliai , AM , Logrieco , A and Sabatini , MA . 2002 . Effects of beauvericin on Schizaphis graminum (Aphididae) . J Invertebrate Pathol , 80 : 90 – 96 .
   PubMed Web of Science ®Google Scholar
• Gäumann , E , Naef-Roth , S and Kern , H . 1960 . Zur phytotoxischen wirksamkeit der enniatine . Phytopathol Zeitschrift , 40 : 45 – 51 .
   Google Scholar
• Grove , JF and Pople , M . 1980 . The insecticidal activity of beauvericin and the enniatin complex . Mycopathologia , 70 : 103 – 105 .
   Web of Science ®Google Scholar
• Gupta , S , Krasnoff , B , Underwood , NL , Renwick , JAA and Roberts , DW . 1991 . Isolation of beauvericin as an insect toxin from Fusarium semitectum and Fusarium moniliforme var. subglutinans . Mycopathologia , 115 : 185 – 189 .
   PubMed Web of Science ®Google Scholar
• Hamill , RL , Higgens , CE , Boaz , HE and Gorman , M . 1969 . The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina . Tetrahedron Lett , 49 : 4255 – 4258 .
   Google Scholar
• Herrmann , M , Zocher , R and Haese , A . 1996 . Enniatin production by Fusarium strains and its effect on potato tuber tissue . Appl Environ Microbiol , 62 : 393 – 398 .
   PubMed Web of Science ®Google Scholar
• Jestoi , MN , Paavanen-Huhtala , S , Parikka , P and Yli-Mattila , T . 2006 . In vitro and in vivo mycotoxin production of Fusarium species isolated from Finnish grains . Archiv Phytopathol Plant Protect , 1 : 1 – 14 .
   Google Scholar
• Jestoi , MN , Rokka , M , Yli-Mattila , T , Parikka , P , Rizzo , A , Ritieni , A and Peltonen , K . 2004 . Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in Finnish grain samples . Food Addit Contam , 21 : 794 – 802 .
   PubMedGoogle Scholar
• Josephs , RD , Krska , R , Schuhmacher , R and Grasserbauer , MA . 1999 . Rapid method for the determination of the Fusarium mycotoxin beauvericin in maize . Fresenius J Analyt Chem , 363 : 130 – 131 .
   Google Scholar
• Kostecki , M , Wisniewska , H , Perrone , G , Ritieni , A , Golinski , P , Chelkowski , J and Logrieco , A . 1999 . The effects of cereal substrate and temperature on production of beauvericin, moniliformin, and fusaproliferin by Fusarium subglutinans ITEM-1434 . Food Addit Contam , 16 : 361 – 365 .
   PubMed Web of Science ®Google Scholar
• Lee , HS , Song , HH , Jung , JH , Shin , CG , Choi , SU and Lee , C . 2008 . Cytotoxicities of enniatins H, I, and MK1688 from Fusarium oxysporum KFCC 11363P . Toxicon , 51 : 1178 – 1185 .
   PubMed Web of Science ®Google Scholar
• Lemmens-Gruber , R , Rachoy , B , Steininger , E , Kouri , K , Saleh , P , Krska , R , Josephs , R and Lemmens , M . 2000 . The effect of the Fusarium metabolite beauvericin on electromechanical and physiological properties in isolated smooth and heart muscle preparations of guinea pigs . Mycopathologia , 149 : 5 – 12 .
   PubMed Web of Science ®Google Scholar
• Lin , Y , Wang , J , Wu , XY , Zhou , SN , Vrijmoed , LLP and Jones , EBG . 2002 . A novel compound enniatin G from the mangrove fungus Halosarpheia sp. from the South China Sea . Austr J Chem , 55 : 225 – 227 .
   Web of Science ®Google Scholar
• Logrieco , A , Moretti , A , Castella , G , Kostecki , M , Golinski , P , Ritieni , A and Chelkowski , J . 1998 . Beauvericin production by Fusarium species . Appl Environ Microbiol , 64 : 3084 – 3088 .
   PubMed Web of Science ®Google Scholar
• Logrieco , A , Moretti , A , Fornelli , F , Fogliano , V , Ritieni , A , Caiaffa , MF , Randazzo , G , Bottalico , A and Macchia , L . 1996 . Fusaproliferin production by Fusarium subglutinans and its toxicity to Artemin salina, SF-9 insect cells, and IARC/LCL 171 human B lymphocytes . Appl Environ Microbiol , 62 : 3378 – 3384 .
   PubMed Web of Science ®Google Scholar
• Logrieco , A , Moretti , A , Ritieni , A , Bottalico , A and Corda , P . 1995 . Occurrence and toxigenicity of Fusarium proliferatum from preharvest maize ear rot, and associated mycotoxins, in Italy . Plant Dis , 79 : 727 – 731 .
   Web of Science ®Google Scholar
• Logrieco , A , Moretti , A , Ritieni , A , Chelkowski , J , Altomare , C , Bottalico , A and Randazzo , G . 1993 . Natural occcurence of beauvericin in preharvest Fusarium subglutinans infected corn ears in Poland . J. Agric. Food Chem , 41 : 2149 – 2152 .
   Web of Science ®Google Scholar
• Logrieco , A , Ritieni , A , Moretti , A , Randazzo , G and Bottalico , A . 1997 . Beauvercicin and fusaproliferin: new emerging Fusarium toxins . Paper presented at the 5th European Fusarium Seminar , 25 : 407 – 412 .
   Google Scholar
• Logrieco , A , Rizzo , A , Ferracane , R and Ritieni , A . 2002 . Occurrence of beauvericin and enniatins in wheat affected by Fusarium avenaceum head blight . Appl Environ Microbiol , 68 : 82 – 85 .
   PubMed Web of Science ®Google Scholar
• Macchia , L , Caiffa , MF , Fornelli , F , Caló , L , Nenna , S , Moretti , A , Logrieco , A and Tursi , A . 2002 . Apoptosis induced by the Fusarium mycotoxin beauvericin in mammalian cells . J Appl Genet , 43 : 363 – 371 .
   Google Scholar
• Marasas , WFO , Thiel , PG , Rabie , CJ , Combrick , PE and Toussoun , TA . 1986 . Moniliformin production in Fusarium section Liseola . Mycologia , 78 : 242 – 247 .
   Web of Science ®Google Scholar
• Mirocha , CJ , Abbas , HK , Windels , CE and Xie , W . 1989 . Variation in deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, and zearalenone production by Fusarium graminearum . Appl Environ Microbiol , 55 : 1315 – 1316 .
   PubMed Web of Science ®Google Scholar
• Moretti , A , Belisario , A , Tafuri , A , Ritieni , A , Corazza , L and Logrieco , A . 2002 . Production of beauvericin by different races of Fusarium oxysporum f. sp. melonis, the Fusarium wilt agent of muskmelon . Eur J Plant Pathol , 108 : 661 – 666 .
   Web of Science ®Google Scholar
• Moretti , A , Logrieco , A , Bottalico , A and Randazzo , G . 1994 . Production of beauvericin by Fusarium proliferatum from maize in Italy . Mycotox Res , 10 : 73 – 78 .
   PubMedGoogle Scholar
• Moretti , A , Logrieco , A , Bottalico , A , Ritieni , A , Randazzo , G and Corda , P . 1995 . Beauvericin production by Fusarium subglutinans from different geographical areas . Mycological Res , 99 : 282 – 286 .
   Web of Science ®Google Scholar
• Munkvold , G , Stahr , HM , Logrieco , A , Moretti , A and Ritieni , A . 1998 . Occurrence of fusaproliferin and beauvericin in Fusarium-contaminated Livestock Feed in Iowa . Appl Environ Microbiol , 64 : 3923 – 3926 .
   PubMed Web of Science ®Google Scholar
• Nelson , PE , Plattner , RD , Shackelford , DD and Desjardins , AE . 1991 . Production of fumonisins by Fusarium moniliforme strains from various substrates and geographic areas . Appl Environ Microbiol , 57 : 2410 – 2412 .
   PubMed Web of Science ®Google Scholar
• Ngoka , LCM , Gross , ML and Toogood , PL . 1999 . Sodium-directed selective cleavage of lactones: a method for structure determination of cyclodepsipeptides . Int J Mass Spectrom , 182 : 289 – 298 .
   Web of Science ®Google Scholar
• Nilanonta , C , Isaka , M , Kittakoop , P , Trakulnaleamsai , S , Tanticharoen , M and Thebtaranonth , Y . 2003 . Unusual enniatins produced by the insect pathogenic fungus Verticillium hemipterigenum: isolation and studies on precursor-directed biosynthesis . Tetrahedron , 59 : 1015 – 1020 .
   Web of Science ®Google Scholar
• Ojcious , DM , Zychlinsky , A , Zheng , LM and Young , JDE . 1991 . Ionophore-induced apoptosis: role of DNA fragmentation and calcium fluxes . Experiment Cell Res , 197 : 43 – 49 .
   PubMed Web of Science ®Google Scholar
• Ramirez , ML , Chulze , S and Magan , N . 2006 . Temperature and water activity effects on growth and temporal deoxynivalenol production by two Argentinean strains of Fusarium graminearum on irradiated wheat grain . Int J Food Microbiol , 106 : 291 – 296 .
   PubMed Web of Science ®Google Scholar
• Sewram , V , Nieuwoudt , TW , Marasas , WF , Shephard , GS and Ritieni , A . 1999 . Determination of the Fusarium mycotoxins, fusaproliferin and beauvericin by high-performance liquid chromatography-electrospray ionization mass spectrometry . J Chromatograph. A , 858 : 175 – 185 .
   PubMed Web of Science ®Google Scholar
• Shemyakin , MM , Ovchinnikov , YU , Ivanov , VT and Kiryushkin , AA . 1963 . The structure of enniatins and related antibiotics . Tetrahedron , 19 : 581 – 591 .
   PubMed Web of Science ®Google Scholar
• Sherwood , RF and Peberdy , JF . 1972 . Factors affecting the production of zearalenone by Fusarium graminearum in grain . J Stored Prod Res , 8 : 71 – 74 .
   Web of Science ®Google Scholar
• Song , HH , Ahn , JH , Lim , YH and Lee , C . 2006 . Analysis of beauvercin and unusual enniatins co-produced by Fusarium oxysporum FB1501 (KFCC 11363P) . J Microbiol Biotechnol , 16 : 1111 – 1119 .
   Web of Science ®Google Scholar
• Song , HH , Lee , HS , Jeong , JH , Park , HS and Lee , C . 2008 . Diversity in beauvericin and enniatins H, I, and MK1688 by Fusarium oxysporum isolated from potato . J Int Food Microbiol , 122 : 296 – 301 .
   PubMed Web of Science ®Google Scholar
• Tomoda , H , Huang , XH , Cao , J , Nishida , H , Nagao , R , Okuda , S , Tanaka , H and Mura , SO . 1992a . Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics . J Antibiot , 45 : 1626 – 1632 .
   PubMed Web of Science ®Google Scholar
• Tomoda , H , Nishida , H , Huang , XX , Masuma , R , Kim , YK and Omura , S . 1992b . New cyclodpsipeptides, enniatins D, E, and F produced by Fusarium sp. FO-1305 . J Antibiot , 45 : 1207 – 1215 .
   PubMed Web of Science ®Google Scholar
• Uhlig , S and Ivanova , L . 2004 . Determination of beauvericin and four other enniatins in grain by liquid chromatography mass spectrometry . J Chromatograph. A , 1050 : 173 – 178 .
   PubMed Web of Science ®Google Scholar